A polyphenol with diverse biological activities
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5-O-Caffeoylshikimic Acid

Item No. 45453

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4R,5R)-5-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid
CAS Number
73263-62-4
Synonyms
  • 5OCSA
Molecular Formula
C16H16O8
Formula Weight
336.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
OC(C(C[C@H]1OC(/C=C/C2=CC(O)=C(O)C=C2)=O)=C[C@H]([C@H]1O)O)=O
InChi Code
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
InChi Key
QMPHZIPNNJOWQI-GDDAOPKQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    5-O-Caffeoylshikimic acid is a polyphenol originally isolated from P. aquilinum that has diverse biological activities.1,2,3 It inhibits xanthine oxidase (XO) in a cell-free assay (IC50 = 13.96 µM).2 In vivo, 5-O-caffeoylshikimic acid decreases serum uric acid, serum creatinine, and blood urea nitrogen levels, renal TNF-α, IL-1β, IL-6, and IL-18 levels, and renal tubular dilation in a mouse model of hyperuricemia induced by potassium oxonate (oxonic acid; Item No. 22586) and hypoxanthine (Item No. 22254). 5-O-Caffeoylshikimic acid is active against S. aureus (MIC = 372 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fukuoka, M. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor. Chem. Pharm. Bull. 30(9), 3219-3224 (1982).

    2. Zhang, D., Zhao, M., Li, Y., et al. Natural xanthine oxidase inhibitor 5-O-caffeoylshikimic acid ameliorates kidney injury caused by hyperuricemia in mice. Molecules 26(23), 7307 (2021).

    3. Khaligh, P., Salehi, P., Farimani, M.M., et al. Bioactive compounds from Smilax excelsa L. J. Iran Chem. Soc. 13, 1055-1059 (2016).